3
˚
˚
b 5 21.9946(12), c 5 11.5867(7) A, b 5 106.399(3)u, U 5 1978.0(2) A ,
5 M. W. Davies, R. A. J. Wybrow, C. N. Johnson and J. P. A. Harrity,
Chem. Commun., 2001, 1558; J. E. Moore, K. M. Goodenough,
D. Spinks and J. P. A. Harrity, Synlett, 2002, 2071; J. E. Moore,
M. W. Davies, K. M. Goodenough, R. A. J. Wybrow, M. York,
C. N. Johnson and J. P. A. Harrity, Tetrahedron, 2005, 61, 6707;
M. D. Helm, J. E. Moore, A. Plant and J. P. A. Harrity, Angew. Chem.,
Int. Ed., 2005, 44, 3889.
6 M. W. Davies, C. N. Johnson and J. P. A. Harrity, Chem. Commun.,
1999, 2107; M. W. Davies, C. N. Johnson and J. P. A. Harrity, J. Org.
Chem., 2001, 66, 3525.
Z 5 4, Dc 5 1.401 Mg m23, space group P21/c (P21/c Ch, No.14), Mo-K a
radiation (l 5 0.71073 A), m(Mo-K a) 5 2.099 mm21, F(000) 5 856. 3641
˚
independent reflections exceeded the significance level |F|/s(|F|) . 4.0.
Refinement converged at a final R 5 0.0627 (wR2 5 0.1546, for all 4548
data, 309 parameters, mean and maximum d/s 0.000, 0.000) with allowance
for the thermal anisotropy of all non-hydrogen atoms. CCDC 608270. For
crystallographic data in CIF or other electronic format see DOI: 10.1039/
b607322k
7 J. E. Moore, M. York and J. P. A. Harrity, Synlett, 2005, 860.
8 K. Afarinkia, V. Vinader, T. D. Nelson and G. H. Posner, Tetrahedron,
1992, 48, 9111 and references cited therein.
9 A. Evnin and D. Seyferth, J. Org. Chem., 1967, 32, 952; D. Seyferth and
D. White, J. Organomet. Chem., 1972, 32, 119.
10 A. Haneda, H. Uenakai, T. Imagawa and M. Kawanisi, Synth.
Commun., 1976, 6, 141; F. Effenberger and T. Ziegler, Chem. Ber., 1987,
120, 1339; T. Ziegler, M. Layh and F. Effenberger, Chem. Ber., 1987,
120, 1347; T. Kitamura, K. Wasai, M. Todaka and Y. Fujiwara,
Synlett, 1999, 731.
11 C. G. Cho, Y. W. Kim, Y. K. Lim, J. S. Park, H. Lee and S. Koo,
J. Org. Chem., 2002, 67, 290; C. G. Cho, Y. W. Kim and W. K. Kim,
Tetrahedron Lett., 2001, 42, 8193.
12 I. W. Ashworth, M. C. Bowden, B. Dembofsky, D. Levin, W. Moss,
E. Robinson, N. Szczur and J. Virica, Org. Process Res. Dev., 2003, 7,
74.
13 Notably, synthesis of a compound analogous to 16 was attempted by
heating 10 with diphenylacetylene at 170 uC for 2 days, however, only a
trace amount of the cycloadduct was observed.
1 Boronic acids, ed. D. G. Hall, Wiley-VCH, Weinheim, 2005.
2 H. Gilman and L. O. Moore, J. Am. Chem. Soc., 1958, 80, 3609;
H. Gilman, L. Santucci, D. R. Swayampati and R. D. Ranck, J. Am.
Chem. Soc., 1957, 79, 3077; K. T. Wong, Y. Y. Chien, Y. L. Liao,
C. C. Lin, M. Y. Chou and M. K. Leung, J. Org. Chem., 2002, 67, 1041
and references cited therein; T. Ishiyama, M. Murata and N. Miyaura,
J. Org. Chem., 1995, 60, 7508; T. Ishiyama, K. Ishida and N. Miyaura,
Tetrahedron, 2001, 57, 9813.
3 T. M. Boller, J. M. Murphy, M. Hapke, T. Ishiyama, N. Miyaura and
J. F. Hartwig, J. Am. Chem. Soc., 2005, 127, 14263; D. N. Coventry,
A. S. Bastanov, A. E. Goeta, J. A. K. Howard, T. B. Marder and
R. N. Perutz, Chem. Commun., 2005, 2172; J. Y. Cho, C. N. Iverson and
M. R. Smith, III, J. Am. Chem. Soc., 2000, 122, 12868 and references
cited therein.
4 G. Hilt and P. Bolze, Synthesis, 2005, 2091; G. Hilt, W. Hess and
F. Schmidt, Eur. J. Org. Chem., 2005, 2526; G. Hilt and K. I. Smolko,
Angew. Chem., Int. Ed., 2003, 42, 2795; G. Hilt, S. Luers and
K. I. Smolko, Org. Lett., 2005, 7, 251.
This journal is ß The Royal Society of Chemistry 2006
Chem. Commun., 2006, 3323–3325 | 3325